N-Iodosuccinimide → HCID 69211817, compound

HRID 2252046Notes

Reaction equation

HRID 2252046 reaction equation
[CH3:1][O:2][C:3]1[CH:29]=[CH:28][C:6]([CH2:7][N:8]2[CH:12]=[C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[N:10]=[C:9]2[CH2:19][O:20][Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22])=[CH:5][CH:4]=1.[I:30]N1C(=O)CCC1=O>CC#N.CCOCC>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]2[C:12]([I:30])=[C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[N:10]=[C:9]2[CH2:19][O:20][Si:21]([C:24]([CH3:26])([CH3:25])[CH3:27])([CH3:22])[CH3:23])=[CH:28][CH:29]=1

Participants

5

Reactant 2

HCID 120273N-IodosuccinimideHCID 69212167HCID 69212167, compound

Product 1

HCID 69211817HCID 69211817, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Procedure

Treat a solution of 1-(4-methoxybenzyl)-2-tert-butyldimethylsilyloxymethyl-4-phenylimidazole (2.08 g, 5.09 mmol) in MeCN (25 mL) with N-iodosuccinimide (NIS) (1.35 g, 6.00 mmol) at room temperature for 24 hours. Dilute the mixture with Et2O (100 mL), wash with saturated NaHCO3 (25 mL), dry (Na2SO4), and concentrate in vacuo. Purify the residue by flash chromatography (SiO2, hexane/EtOAc 20:1→9:1) to provide 2.30 g (85% yield). MS (ES+): m/z 535 (M+H)+

Workup

  1. washwash with saturated NaHCO3 (25 mL)
  2. dry with materialdry (Na2SO4)
  3. concentrationconcentrate in vacuo
  4. customPurify the residue by flash chromatography (SiO2, hexane/EtOAc 20:1→9:1)
  5. customto provide 2.30 g (85% yield)

Sources & evidence

ORD record
ord-a16ee3fa70114f07a75b9bf5d2b0366c
Source dataset
uspto-grants-2008_01
Patent number
US07320995B2

Reaction notes

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